3,3,3-trifluoropropionyl chloride is an extremely important compound as an intermediate of medicines and agricultural chemicals and as a production raw material or synthesis intermediate of functional materials such as fluorine-containing polymers. Hitherto, the following production processes have been reported.
In general, as a process for producing a carboxylic chloride, there is known a process of making the corresponding carboxylic acid into a carboxylic chloride by a chlorinating agent, such as thionyl chloride, phosphorus oxychloride, and phosphorus pentachloride.
As a process for producing 3,3,3-trifluoropropionyl chloride, Non-patent Publication 1 discloses a process in which CF3(CH2)2Cl is turned into a Grignard compound, followed by oxidation to obtain CF3(CH2)2OH, and this is oxidized by chromic acid into 3,3,3-trifluoropropionic acid, followed by chlorination by phosphorus pentachloride to obtain 3,3,3-trifluoropropionyl chloride.
Non-patent Publication 2 discloses a process for obtaining 3,3,3-trifluoropropionyl chloride by chlorinating 3,3,3-trifluoropropionic acid with phthaloyl chloride.
Furthermore, there are known processes of turning fluorine atom-free, aromatic aldehydes and hydrocarbonaceous aldehydes into carboxylic bromides by N-bromo compounds such as N-bromosuccinic imide (Non-patent Publications 3-6). In particular, it is known that a compound, such as an aromatic aldehyde, having no hydrogen at α-position of a carbonyl carbon (α-position herein refers to a carbon site adjacent to the carbonyl carbon) is chlorinated by chlorine to give the corresponding carboxylic chloride (Non-patent Publication 7).
Non-patent Publication 1: Journal of the American Chemical Society, Vo. 77, pp. 1901-1902, the year 1955
Non-patent Publication 2: Journal of Fluorine Chemistry, Vol. 86, pp. 99-104, the year 1997
Non-patent Publication 3: Journal of the Chemical Society of Japan, Vol. 77, pp. 591-594, the year 1956
Non-patent Publication 4: Journal of the Chemical Society of Japan, Vol. 79, pp. 487-490, the year 1958
Non-patent Publication 5: Tetrahedron Letters, Vol. 20, pp. 3809-3810, the year 1979
Non-patent Publication 6: Tetrahedron Letters, Vol. 31, pp. 7237-7240, the year 1990
Non-patent Publication 7: Organic Syntheses, Coll. Vol. 1, p. 155, the year 1941